Intramolecular vinyl quinone Diels-Alder reactions: Asymmetric entry to the cordiachrome core and synthesis of (-)-isoglaziovianol

Florian Löbermann; Lara Weisheit; Dirk Trauner

doi:10.1021/ol401787n

Intramolecular vinyl quinone Diels-Alder reactions: Asymmetric entry to the cordiachrome core and synthesis of (-)-isoglaziovianol

Florian Löbermann, Lara Weisheit, Dirk Trauner

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A short and asymmetric entry to the core structure of the cordiachromes has been developed, allowing access to (-)-isoglaziovianol in seven steps. Our synthesis includes a Trost asymmetric allylic alkylation and a reaction cascade triggered by a vinyl quinone Diels-Alder reaction and followed by intramolecular nucleophilic interception.

Original language	English (US)
Pages (from-to)	4324-4326
Number of pages	3
Journal	Organic Letters
Volume	15
Issue number	17
DOIs	https://doi.org/10.1021/ol401787n
State	Published - Sep 6 2013

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol401787n

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abstract = "A short and asymmetric entry to the core structure of the cordiachromes has been developed, allowing access to (-)-isoglaziovianol in seven steps. Our synthesis includes a Trost asymmetric allylic alkylation and a reaction cascade triggered by a vinyl quinone Diels-Alder reaction and followed by intramolecular nucleophilic interception.",

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AU - Löbermann, Florian

AU - Weisheit, Lara

AU - Trauner, Dirk

PY - 2013/9/6

Y1 - 2013/9/6

N2 - A short and asymmetric entry to the core structure of the cordiachromes has been developed, allowing access to (-)-isoglaziovianol in seven steps. Our synthesis includes a Trost asymmetric allylic alkylation and a reaction cascade triggered by a vinyl quinone Diels-Alder reaction and followed by intramolecular nucleophilic interception.

AB - A short and asymmetric entry to the core structure of the cordiachromes has been developed, allowing access to (-)-isoglaziovianol in seven steps. Our synthesis includes a Trost asymmetric allylic alkylation and a reaction cascade triggered by a vinyl quinone Diels-Alder reaction and followed by intramolecular nucleophilic interception.

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Intramolecular vinyl quinone Diels-Alder reactions: Asymmetric entry to the cordiachrome core and synthesis of (-)-isoglaziovianol

Abstract

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